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WO2008113881B1 - Compound that is a dual inhibitor of enzymes pde7 and/or pde4, pharmaceutical compositions and uses thereof - Google Patents

Compound that is a dual inhibitor of enzymes pde7 and/or pde4, pharmaceutical compositions and uses thereof

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Publication number
WO2008113881B1
WO2008113881B1 PCT/ES2008/070051 ES2008070051W WO2008113881B1 WO 2008113881 B1 WO2008113881 B1 WO 2008113881B1 ES 2008070051 W ES2008070051 W ES 2008070051W WO 2008113881 B1 WO2008113881 B1 WO 2008113881B1
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WO
WIPO (PCT)
Prior art keywords
methylthio
oxo
dihydroquinazoline
thioxo
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/ES2008/070051
Other languages
Spanish (es)
French (fr)
Other versions
WO2008113881A1 (en
Inventor
Ayuso-Gontan Carmen Gil
Calduch Tania Castano
Martin Nuria Campillo
Jareno Sara Ballester
Garcia Coral Gonzalez
Torres Francisco Javier Hernandez
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Consejo Superior de Investigaciones Cientificas CSIC
Instituto de Salud Carlos III
Original Assignee
Consejo Superior de Investigaciones Cientificas CSIC
Instituto de Salud Carlos III
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Publication date
Application filed by Consejo Superior de Investigaciones Cientificas CSIC, Instituto de Salud Carlos III filed Critical Consejo Superior de Investigaciones Cientificas CSIC
Priority to CA002682259A priority Critical patent/CA2682259A1/en
Priority to JP2010500305A priority patent/JP2010522226A/en
Priority to US12/532,104 priority patent/US20100152213A1/en
Priority to EP08736738A priority patent/EP2130823A4/en
Priority to AU2008228203A priority patent/AU2008228203A1/en
Priority to CN200880013379A priority patent/CN101679314A/en
Publication of WO2008113881A1 publication Critical patent/WO2008113881A1/en
Publication of WO2008113881B1 publication Critical patent/WO2008113881B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • C07D239/96—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Rheumatology (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Dermatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Transplantation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention relates to a series of dual inhibitors of enzymes PDE7 and PDE4, having formula (I) and to the use thereof in the production of pharmaceutical compositions for the treatment of inflammatory and/or autoimmune processes.

Claims

44REIVINDICACIONES MODIFICADAS recibidas por Ia oficina Internacional el 04 de septiembre de 2008 (04.09.2008)REIVINDICACIONES 44 MODIFIED REVINDICATIONS received by the International Office on September 4, 2008 (04.09.2008) CLAIMS 1.- Uso de al menos un compuesto de fórmula (I), con actividad inhibidora dual de las enzimas PDE7 y/o PDE4, junto con un portador, adyuvante o vehículo farmacéuticamente aceptable, para Ia elaboración de una composición farmacéutica o medicamento útil para el tratamiento de enfermedades inflamatorias o autoinmunes, siendo Ia fórmula (I):1. Use of at least one compound of formula (I), with dual inhibitory activity of PDE7 and / or PDE4 enzymes, together with a carrier, adjuvant or pharmaceutically acceptable vehicle, for the preparation of a pharmaceutical composition or drug useful for the treatment of inflammatory or autoimmune diseases, the formula (I) being:
Figure imgf000002_0001
Figure imgf000002_0001
 donde:where: A, es un carbociclo o heterociclo fusionado opcionalmente sustituido de 5, 6 ó 7 miembros saturado o insaturado, puede ser un doble enlace; X e Y, son elegidos independientemente entre el grupo consistente en hidrógeno, alquil, =0, =S, aril, O-alquil, O-aril, S-alquil o -S-aril; yA, is an optionally substituted saturated or unsaturated 5, 6 or 7 membered carbocycle or optionally substituted fused heterocycle, may be a double bond; X and Y, are independently chosen from the group consisting of hydrogen, alkyl, = 0, = S, aryl, O-alkyl, O-aryl, S-alkyl or -S-aryl; Y R, R1, R2 y R3 son elegidos independientemente entre el grupo consistente en hidrógeno, halógeno, alquil, haloalquil, aril, cicloalquil, (CHb)n- aril, heteroaril, -OR3; -C(O)OR3, (CH2)n-C(O)OR3 o -S(O)4-, dónde n es mayor o igual a 0 y dónde t es 1 o 2,R, R 1 , R 2 and R 3 are independently chosen from the group consisting of hydrogen, halogen, alkyl, haloalkyl, aryl, cycloalkyl, (CHb) n -aryl, heteroaryl, -OR 3 ; -C (O) OR 3 , (CH 2 ) n -C (O) OR 3 or -S (O) 4 -, where n is greater than or equal to 0 and where t is 1 or 2, o bien una sal, derivado, profármaco, solvato o estereoisómero farmacéuticamente aceptables del mismo, donde el término "derivado" incluye tanto a compuestos farmacéuticamente aceptables, es decir, derivados del compuesto de fórmula (I) que pueden ser utilizados en Ia elaboración de un medicamento, como derivados farmacéuticamente no aceptables ya que éstos pueden ser útiles en Ia preparación de derivados farmacéuticamente aceptables, y dónde el término "profármaco" incluye a cualquier compuesto derivado de un compuesto de fórmula (I), que, ventajosamente, aumenta Ia biodisponibilidad del compuesto de fórmula (I) cuando se administra a un 45or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof, wherein the term "derivative" includes both pharmaceutically acceptable compounds, ie, derivatives of the compound of formula (I) that can be used in the preparation of a medicament, as pharmaceutically acceptable derivatives, since these may be useful in the preparation of pharmaceutically acceptable derivatives, and where the term "prodrug" includes any compound derived from a compound of formula (I), which, advantageously, increases the bioavailability of the compound of formula (I) when administered to a Four. Five individuo o que potencia Ia liberación del compuesto de fórmula (I) en un compartimento biológico.individual or that enhances the release of the compound of formula (I) in a biological compartment. Excepción: cuando A sea benceno sin sustituir, X=O1Y=S cuando A sea benceno sin sustituir, X=O1Y=O, cuando A sea benceno sin sustituir, X=O1Y=S-Me cuando A sea tiofeno sin sustituir, X=O1Y=S, y cuando A sea benzotiofeno sin sustituir, X=O,Y=SException: when A is unsubstituted benzene, X = O 1 Y = S when A is unsubstituted benzene, X = O 1 Y = O, when A is unsubstituted benzene, X = O 1 Y = S-Me when A is unsubstituted thiophene, X = O 1 Y = S, and when A is unsubstituted benzothiophene, X = O, Y = S 2.- Compuesto según Ia reivindicación 1 caracterizado porque presenta Ia fórmula 2-metilt¡o-4-tioxo-3,4-dihidroqu¡nazolina (Compuesto Id).2. Compound according to claim 1, characterized in that it has the formula 2-methylthio-4-thioxo-3,4-dihydroquinoline (Compound Id). 3.- Compuesto según Ia reivindicación 2 caracterizado porque pertenece al siguiente grupo: - 3-Fenil-2-metiltio-4-tioxo-3,4-dihidroquinazolina,3. Compound according to claim 2, characterized in that it belongs to the following group: - 3-Phenyl-2-methylthio-4-thioxo-3,4-dihydroquinazoline, - 3-(2,6-difluorofenil)-2-metiltio-4-tioxo-3,4-dih¡droquinazolina,3- (2,6-difluorophenyl) -2-methylthio-4-thioxo-3,4-dihydroquinazoline, - 3-(2,3,4-trifluorofenil)-2 metiltio-4-tioxo-3,4-dihidroquinazolina, y - 3-(2-bromofenil)-2-metilt¡o-4-t¡oxo-3,4-dihidroquinazol¡na.3- (2,3,4-trifluorophenyl) -2-methylthio-4-thioxo-3,4-dihydroquinazoline, and -3- (2-bromophenyl) -2-methylthio-4-t -oxo-3, 4-dihydroquinazoline. 4.- Composición farmacéutica caracterizada porque comprende un compuesto, en cantidad terapéuticamente efectiva, de fórmula (I), o mezclas de los mismos, una sal, derivado, profármaco, solvato o estereoisómero farmacéuticamente aceptable del mismo junto con un portador, adyuvante o vehículo farmacéuticamente aceptable, para Ia administración a un paciente.4. Pharmaceutical composition characterized in that it comprises a compound, in therapeutically effective amount, of formula (I), or mixtures thereof, a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof together with a carrier, adjuvant or vehicle pharmaceutically acceptable, for the administration to a patient. 5.- Composición farmacéutica según Ia reivindicación 4 caracterizado porque el compuesto de formula (I) pertenece a una, o a varias, de las siguientes familias de compuestos:5. Pharmaceutical composition according to claim 4, characterized in that the compound of formula (I) belongs to one or more of the following families of compounds: - 4-oxo-2-tioxo-1 ,2,3,4-tetrahidroquinazolina (Compuesto Ia), - 2-metiltio-4-oxo-3,4-dihidroquinazolina (Compuesto Ib),- 4-Oxo-2-thioxo-1, 2,3,4-tetrahydroquinazoline (Compound Ia), - 2-methylthio-4-oxo-3,4-dihydroquinazoline (Compound Ib), - 2,4-ditioxo-1 ,2,3,4-tetrahidroquinazolina (Compuesto Ic), y2,4-dithioxo-1, 2,3,4-tetrahydroquinazoline (Compound Ic), and - 2-metiltio-4-tioxo-3,4-dihidroquinazolina (Compuesto Id), 46- 2-methylthio-4-thioxo-3,4-dihydroquinazoline (Compound Id), 46 O a cualquiera de sus formas enantioméricas R, S y/o mezclas racémicas.Or to any of its enantiomeric forms R, S and / or racemic mixtures. 6.- Composición farmacéutica según Ia reivindicación 5 caracterizado porque el compuesto o mezcla de compuestos de formula (I) pertenece al siguiente grupo:6. Pharmaceutical composition according to claim 5, characterized in that the compound or mixture of compounds of formula (I) belongs to the following group: - 6-Bromo-3-fenil-4-oxo-2-tioxo-1 ,2,3,4-tetrahidroquinazolina, - 6-Bromo-3-(2,6-difluorofenil)-4-oxo-2-tioxo-1 ,2,3,4-tetrahidroquinazolina,- 6-Bromo-3-phenyl-4-oxo-2-thioxo-1, 2,3,4-tetrahydroquinazoline, - 6-Bromo-3- (2,6-difluorophenyl) -4-oxo-2-thioxo- 1, 2,3,4-tetrahydroquinazoline, 6-Bromo-3-(2,3,4-trifluorofen¡l)-4-oxo-2-tioxo-1 ,2,3,4- tetrahidroquinazolina,6-Bromo-3- (2,3,4-trifluorophenol) -4-oxo-2-thioxo-1, 2,3,4-tetrahydroquinazoline, - 6-Bromo-3-(2-bromofenil)-4-oxo-2-tioxo-1 ,2,3,4-tetrahidroquinazolina, - 3-(2,6-Difluorofenil)-8-metil-4-oxo-2-tioxo-1,2,3,4-tetrahidroquinazolina, - 3-(2,3,4-Trifluorofenil)-8-metil-4-oxo-2-tioxo-1 ,2,3,4-tetrahidroqu¡nazolina, - 3-(2-Bromofenil)-8-metil-4-oxo-2-tioxo-1 ,2,3,4-tetrahidroquinazolina, - 6-Bromo-3-fenil-2-metiltio-4-oxo-3,4-dih¡droquinazolina,- 6-Bromo-3- (2-bromophenyl) -4-oxo-2-thioxo-1, 2,3,4-tetrahydroquinazoline, -3- (2,6-difluorophenyl) -8-methyl-4-oxo- 2-thioxo-1,2,3,4-tetrahydroquinazoline, 3- (2,3,4-trifluorophenyl) -8-methyl-4-oxo-2-thioxo-1, 2,3,4-tetrahydroquinoline , - 3- (2-Bromophenyl) -8-methyl-4-oxo-2-thioxo-1, 2,3,4-tetrahydroquinazoline, - 6-Bromo-3-phenyl-2-methylthio-4-oxo-3 , 4-dihydroquinazoline, - 6-Bromo-3-(2,6-difluorofenil)-2-metiltio-4-oxo-3,4-dihidroquinazolina, - 6-Bromo-3-(2,3,4-trifluorofenil)-2-metiltio-4-oxo-3,4-dihidroquinazolina, - 6-Bromo-3-(2-bromofenil)-2-metiltio-4-oxo-3,4-dihidroquinazolina, - 3-Fenil-8-metil-2-metiltio-4-oxo-3,4-dihidroquinazolina, - 3-(2,6-Difluorofenil)-8-metil-2-metiltio-4-oxo-3,4-dihidroquinazolina,- 6-Bromo-3- (2,6-difluorophenyl) -2-methylthio-4-oxo-3,4-dihydroquinazoline, - 6-Bromo-3- (2,3,4-trifluorophenyl) -2-methylthio- 4-Oxo-3,4-dihydroquinazoline, - 6-Bromo-3- (2-bromophenyl) -2-methylthio-4-oxo-3,4-dihydroquinazoline, - 3-Phenyl-8-methyl-2-methylthio- 4-oxo-3,4-dihydroquinazoline, 3- (2,6-Difluorophenyl) -8-methyl-2-methylthio-4-oxo-3,4-dihydroquinazoline, - 3-(2I3,4-trifluorofenil)-8-metil-2-metiltio-4-oxo-3,4-dih¡droquinazolina, - 3-(2-bromofenil)-8-metil-2-metiltio-4-oxo-3,4-dihidroquinazolina,3- (2 I- 3,4-trifluorophenyl) -8-methyl-2-methylthio-4-oxo-3,4-dihydroquinazoline, 3- (2-bromophenyl) -8-methyl-2-methylthio- 4-oxo-3,4-dihydroquinazoline, - 3-Fenil-2,4-ditioxo-1 ,2,3,4-tetrahidroquinazolina, - 3-(2,6-D¡fluorofenil)-2,4-ditioxo-1 ,2,3,4-tetrahidroquinazolina, - 3-(2,3,4-Tr¡fluorofenil)-2,4-ditioxo-1 ,2,3,4-tetrahidroquinazolina.- 3-Phenyl-2,4-dithioxo-1, 2,3,4-tetrahydroquinazoline, -3- (2,6-D-fluorophenyl) -2,4-dithioxo-1, 2,3,4-tetrahydroquinazoline, 3- (2,3,4-Trifluorophenyl) -2,4-dithioxo-1, 2,3,4-tetrahydroquinazoline. - 3-Fen¡l-2-metiltio-4-tioxo-3,4-dihidroqu¡nazolina, - 3-(2,6-difluorofenil)-2-metiltio-4-tioxo-3,4-dihidroquinazolina,- 3-Phenylt-2-methylthio-4-thioxo-3,4-dihydro-cyzanoline, -3- (2,6-difluorophenyl) -2-methylthio-4-thioxo-3,4-dihydroquinazoline, - 3-(2,3,4-trifluorofenil)-2 metiltio-4-tioxo-3,4-dihidroquinazolina, y - 3-(2-bromofenil)-2-metiltio-4-tioxo-3,4-dihidroquinazolina.3- (2,3,4-trifluorophenyl) -2-methylthio-4-thioxo-3,4-dihydroquinazoline, and -3- (2-bromophenyl) -2-methylthio-4-thioxo-3,4-dihydroquinazoline. 7.- Uso de un compuesto según Ia reivindicación 1 caracterizado porque Ia enfermedad inflamatoria o autoinmune pertenece al siguiente grupo: enfermedad inflamatoria intestinal, patologías articulares inflamatorias, dermatitis atópicas y otras patologías dermatológicas inflamatorias, neuritis, encefalitis, encefalomielitis y patologías inflamatorias que afectan al sistema nervioso central (esclerosis múltiple) o periférico, miositis, vasculitis, lupus eritematoso sistémico, asma, enfermedad pulmonar obstructiva crónica, enfermedades infecciosas que cursan con inflamación, reacciones de rechazo de huésped contra injerto, conjuntivitis y oculopatías inflamatorias, otitis y mucositis. 7. Use of a compound according to claim 1 characterized in that the inflammatory or autoimmune disease belongs to the following group: inflammatory bowel disease, inflammatory joint pathologies, atopic dermatitis and other inflammatory dermatological pathologies, neuritis, encephalitis, encephalomyelitis and inflammatory pathologies affecting the central nervous system (multiple sclerosis) or peripheral, myositis, vasculitis, systemic lupus erythematosus, asthma, obstructive pulmonary disease chronic, infectious diseases that occur with inflammation, reactions of host rejection against graft, conjunctivitis and inflammatory oculopathies, otitis and mucositis.
PCT/ES2008/070051 2007-03-22 2008-03-14 Compound that is a dual inhibitor of enzymes pde7 and/or pde4, pharmaceutical compositions and uses thereof Ceased WO2008113881A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CA002682259A CA2682259A1 (en) 2007-03-22 2008-03-14 Compound that is a dual inhibitor of enzymes pde7 and/or pde4, pharmaceutical compositions and uses thereof
JP2010500305A JP2010522226A (en) 2007-03-22 2008-03-14 Dual inhibitory compounds, pharmaceutical compositions and methods of use of the enzymes PDE7 and / or PDE4
US12/532,104 US20100152213A1 (en) 2007-03-22 2008-03-14 Compound that is a dual inhibitor of enzymes pde7 and/or pde4, pharmaceutical compositions and uses thereof
EP08736738A EP2130823A4 (en) 2007-03-22 2008-03-14 DOUBLE INHIBITOR COMPOUND OF PDE7 AND / OR PDE4 ENZYMES, SPHARMACEUTICAL COMPOSITIONS AND THEIR APPLICATIONS
AU2008228203A AU2008228203A1 (en) 2007-03-22 2008-03-14 Compound that is a dual inhibitor of enzymes PDE7 and/or PDE4, pharmaceutical compositions and uses thereof
CN200880013379A CN101679314A (en) 2007-03-22 2008-03-14 Dual inhibitory compound of enzyme PDE7 and/or PDE4, pharmaceutical composition and use thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ES200700762A ES2308916B1 (en) 2007-03-22 2007-03-22 DUAL INHIBITOR COMPOUND OF PDE7 AND / OR PDE4 ENZYMES, PHARMACEUTICAL COMPOSITIONS AND THEIR APPLICATIONS.
ESP200700762 2007-03-22

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WO2008113881A1 WO2008113881A1 (en) 2008-09-25
WO2008113881B1 true WO2008113881B1 (en) 2008-11-06

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EP2130823A4 (en) 2011-06-15
JP2010522226A (en) 2010-07-01
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